What are the top rated Winter Rentals in Lahaina?

There are a lot of options in Lahaina. If you plan on staying in the Lahaina area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Lahaina: <a href="/property/hokulani-436-corner-unit-2bd-2ba-w-ocean-mountain-views-505sqft-lanai-balcony/HA-121351511" class="class="static-page-link"">HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN &amp; MOUNTAIN VIEWS,505SQFT LANAI BALCONY</a> <a href="/property/mahana-at-kaanapali-spectacular-oceanfront-amazing-sunsets-sea-life-unit1014/HA-3212710861" class="class="static-page-link"">Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets &amp; Sea Life Unit1014</a> <a href="/property/nread-our-reviews-and-see-why-our-guests-love-to-stay-with-us/HA-321149024" class="class="static-page-link"">nRead Our Reviews and See Why Our Guests Love to Stay with Us.</a> <a href="/property/sleep-number-bed-759-1bdrm-a-guest-favorite-ocean-beach-view-w-xbox-roku/HA-321199982" class="class="static-page-link"">SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/XBOX &amp; ROKU!</a> <a href="/property/the-whaler-beautifully-remodeled-ground-floor-courtyard-studio/HA-321610678" class="class="static-page-link"">The Whaler! ~Beautifully remodeled ground floor courtyard studio~</a> <a href="/property/luxury-studio-ocean-view-honua-kai-resort-konea215-pools-beach-access-5-star/HA-3211389817" class="class="static-page-link"">Luxury Studio-Ocean View-Honua Kai Resort Konea215- Pools,Beach Access,5 star</a> <a href="/property/maui-resort-rentals-hokulani-605-premier-6th-floor-oceanview-penthouse-closest-2br-column-to-the-oce/HA-3214785263" class="class="static-page-link"">Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!</a> <a href="/property/mahana-spectacular-11th-floor-corner-with-270-degree-oceanfront-views-2br-2ba/HA-32126208" class="class="static-page-link"">MAHANA SPECTACULAR 11th FLOOR CORNER WITH 270 DEGREE OCEANFRONT VIEWS! 2BR/2BA</a> <a href="/property/nkaanapali-ocean-front-condo-free-parking-and-no-resort-fees-cabana-access/HA-321259621" class="class="static-page-link"">nKaanapali, Ocean Front Condo, Free parking and NO Resort Fee’s, Cabana Access.</a> <a href="/property/views-views/HA-321353835" class="class="static-page-link"">Views! Views!</a>

How much does it cost to rent a place to stay near Lahaina in the wintertime?

The average cost for winter rentals in Lahaina is $1,269 per night. Bigislandhawaiirental has a wide list of great winter places to stay near Lahaina that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Lahaina that allow pets?

Yes, here are the top cottage/chalet rentals in Lahaina that allow you to bring your pet or dog: Breathtaking Transformation! Luxury 3-BR Oceanfront Condo Lahaina Oceanfront Estate-Main House Puunoa - CoralTree Residence Collection 164 Ten Star Reviews out of 164, AMAZING, Maui Magic, A206 with AC, BEACHFRONT See all <a href="/all/usa/hawaii/lahaina/pet-friendly-rentals" class="class=&#34;static-page-link&#34;">pet-friendly vacation rentals in Lahaina</a> on Bigislandhawaiirental

Do you have any winter rentals in Lahaina that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Lahaina to find what works for you.

Are there winter accommodations in Lahaina that have indoor swimming pools?

As of 2026, the data from Bigislandhawaiirental shows that there are over 7200 private swimming pools or indoor pools accommodations near Lahaina along with other great amenities.

Winter Rentals in Lahaina:【 GREAT PRICES 】

Breathtaking Transformation! Luxury 3-BR Oceanfront Condo

From US $1,133

10.0 (174 Reviews)

Condo

Breathtaking Transformation! Luxury 3-BR Oceanfront Condo

Air Conditioner
Parking
Pool

Lahaina Winter Rentals & Holiday Homes

Discover winter rentals Lahaina - We found 7200 exact matches

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